20946-32-1

Basic information

• Product Name: 3,4-Thiophenedicarboxylic acid, 2,5-dihydro-, dimethyl ester
• CAS NO: 20946-32-1
• Molecular Formula: C8H10O4S
• Molecular Weight: 202.231
• Mol File: 20946-32-1.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 3,4-Thiophenedicarboxylic acid, 2,5-dihydro-, dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Thiophenedicarboxylic acid, 2,5-dihydro-, dimethyl ester(20946-32-1)
• EPA Substance Registry System: 3,4-Thiophenedicarboxylic acid, 2,5-dihydro-, dimethyl ester(20946-32-1)

Safety Data

• Hazardous Substances Data: 20946-32-1(Hazardous Substances Data)

Upstream product

• 108579-47-1 bis<(trimethylsilyl)methyl>sulfoxide 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 170945-21-8 methyl 4-{[(trifluoromethyl)sulfonyl]oxy}-2,5-dihydrothiophene-3-carboxylate 
• 2689-68-1 methyl 4-oxotetrahydrothiophene-3-carboxylate 
• 7400-45-5 dimethyl-3-thiaadipate 
• 80356-26-9 (E/Z)-Dimethyl 2,3-bis-butenedioate 
• 13314-92-6 dimethyl (Z)-2,3-dimethyl-2-butenedioate 
• 766-39-2 2,3-Dimethylmaleic anhydride 
• 197161-24-3 thioformaldehyde S-methylide 
• 105850-89-3 chloromethyl (trimethylsilyl)methyl sulfide 
• 20688-07-7 2,2,4,4-tetrahydrothiophene-3,4-dicarboxylic acid 

Downstream Products

• 20688-07-7 2,2,4,4-tetrahydrothiophene-3,4-dicarboxylic acid 
• 945561-47-7 5-phenyl-1,3-dihydro-thieno[3,4-c]pyrrole-4,6-dione 
• 945561-48-8 2,2-dioxo-5-phenyl-2,3-dihydro-1H-2λ⁶-thieno[3,4-c]pyrrole-4,6-dione 
• 945561-49-9 2,6-diphenyl-3a,4,8,8a-tetrahydro-pyrrolo[3,4-f]isoindole-1,3,5,7-tetraone 
• 75532-25-1 2,2,4,4-tetrahydrothiophene-3,4-dicarboxylic acid anhydride 
• 6626-68-2 2,6-diphenyl-pyrrolo[3,4-f]isoindole-1,3,5,7-tetraone 
• 4282-35-3 dimethyl thiophene-3,4-dicarboxylate 
• 4282-29-5 thiophene-3,4-dicarboxylic acid 
• 33527-26-3 thiophene-3,4-dicarboxylic acid chloride 
• 56-25-7 cantharidin 

Relevant articles and documents

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Synthesis of dicarboxylic acid derivatives of [60]fullerene using Diels- Alder reaction with bis(methylene)butanedioates

3-Sulfolene-3,4-dicarboxylates effective for generation of bis(methylene)butanedioates were applied to [4+2] cycloaddition reaction of C60 to give fullerocyclohexenedicarboxylates, among which a t-butyl ester was hydrolyzed to a dicarboxylic acid derivative, useful for further conversion into its anhydride and half-esters. (C) 2000 Elsevier Science Ltd.

SYNTHESIS OF CANTHARIDIN

The invention provides synthetic methods for the preparation of cantharidin and analogs thereof. In one aspect, the invention provides an improved Diels-Alder cycloaddition to generate a key intermediate en route to cantharidin and analogs thereof. In certain embodiments, the new Diels-Alder reaction involves reacting Compound (2) in the presence of furan, and in the absence of acid or increased pressure, in an aprotic polar solvent with slight warming, to yield Compound (1) in favorable yield and exo-endo ratio. In another aspect, the invention also provides a new Diels-Alder reaction between compounds of Formula (III) and furan to yield compounds of Formula (IV), which can then be transformed into cantharidin or analogs thereof. In yet another aspect, the invention describes a new palladium-mediated carbonylation providing another key intermediate en route to cantharidin and analogs thereof. In addition to synthetic methods, present invention also provides compounds {i.e., intermediates) useful in the synthesis of cantharidin and analogs thereof. Compounds provided herein may have biological activity, and therefore may be used in the treatment of diseases or conditions {e.g., infectious diseases and skin conditions).

COMMERCIALLY VIABLE SYNTHESIS OF CANTHARIDIN AND BIOACTIVE CANTHARIDIN DERIVATIVES

The present disclosure provides methods for synthesizing cantharidin and cantharidin derivatives.